Acetyl chloride → 1-(2,3-Dihydro-benzo[b]thiophen-5-yl)-ethanone

HRID 546256

反応式

HRID 546256 の反応式
[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[C:10](Cl)(=[O:12])[CH3:11].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([C:10](=[O:12])[CH3:11])[CH:8]=[CH:9][C:2]1=2

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 783192,3-Dihydrobenzo(b)thiopheneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 122561311-(2,3-Dihydro-benzo[b]thiophen-5-yl)-ethanone収率 78.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-10 °C

実験手順

To a solution of 2,3-dihydro-benzo[b]thiophene (1.88 g, 13.8 mmol) in methylene chloride (20 mL) at −10° C. was added dropwise a solution of acetyl chloride (1.85 mL, 25.9 mmol) and aluminum chloride (1.84 g, 13.8 mmol) in methylene chloride (20 mL) keeping the temperature below −6° C. during the addition period. After the addition is complete the reaction mixture was stirred for an additional 30 min at −10° C. and then added ice (40 mL) and concentrated hydrochloric acid (6 mL) and extracted with methylene chloride (3×20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification on an AnaLogix Intelliflash system (80 g column, 10% diethyl ether/hexanes) afforded 1-(2,3-dihydro-benzo[b]thiophen-5-yl)-ethanone (1.93 g, 78%) as a clear colorless oil.

後処理

  1. customthe temperature below −6° C.
  2. additionduring the addition period
  3. additionAfter the addition
  4. extractionadded ice (40 mL) and concentrated hydrochloric acid (6 mL) and extracted with methylene chloride (3×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification on an AnaLogix Intelliflash system (80 g column, 10% diethyl ether/hexanes)

出典と根拠

ORDレコード
ord-81945bebadd143538357f16eee7e0bfe
出典データセット
uspto-grants-2011_05
特許番号
US07935699B2

関連ノート

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